I think there are two ways to address the first question. One is, which series' third season had the best episodes in terms of Star Trek as a whole? For that, I guess I'd agree it's TNG, though DS9 is a close second. The other is, which series had the strongest third season relative to the rest of that particular series? In that sense, I'd give it to Voyager. Season 3 was my favorite season of VGR, with a lot of strong, solid Star Trek stories. Season 4 was comparably good, but season 3 was the only one that really managed to be the show that Voyager's creators wanted it to be all along -- i.e. a show that was less about the obsession with getting home to the known and familiar and more about embracing the adventure of discovering the new and unknown.

As for who'd be the best person to cheer me up, make me laugh? Definitely not Quark. He's someone you can find funny watching him from a distance, but I think his insincerity, selfishness, and impatience would make him less comforting to someone who actually had to deal with him face to face. Neelix would be much better as a source of cheer and comfort. Yes, he has his idiosyncrasies that can try one's patience, but he's very sincere and genuinely good-natured, and it's a lot easier to believe he'd really have your back when you needed someone.

Dr. Phlox would also be good for a pick-me-up. He's irrepressibly good-natured and a lot of fun. In terms of being intentionally funny and able to make you laugh, though? I'm thinking either Kirk or Jadzia.

Been a while since I've seen all of the Season 3's, so i'll stay out of that part, but for someone funny, I'd probably say Trip on Enterprise. Good storyteller, has plenty of them, and has a pretty quick wit

...either that or go to T'Pol, treat her like the queen's guard at Buckingham Palace and entertain myself trying to get her to laugh/smile

...either that or go to T'Pol, treat her like the queen's guard at Buckingham Palace and entertain myself trying to get her to laugh/smile

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T'Pol actually had a pretty wicked sense of deadpan humor. You'd go up against her at your peril, I think.

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Hmm...I'm in the middle of watching Enterprise the first time through (I'm 2 episodes in on season 4). Maybe I'm biased by the Enterprise Kool-Aid, and I do see how T'Pol can be seen as deadpan, but she comes across to me with the same snide attitude that all Vulcans portray in Enterprise. When she starts losing control of her emotions in the expanse, she still doesn't really get a sense of humor. Don't know yet if this changes in Season 4.

^Well, yes, that's just it -- her snide, acerbic comments are often real zingers. I'm not talking about humor in the sense of laughing at knock-knock jokes, but in the sense of dry sarcasm and biting comebacks. A typical Vulcan would just react with incomprehension or excessive literalism when a human says something illogical or impertinent, but T'Pol will wither them with a sardonic reply. Maybe it's more "wit" than "humor," but it's definitely there.

^Well, yes, that's just it -- her snide, acerbic comments are often real zingers. I'm not talking about humor in the sense of laughing at knock-knock jokes, but in the sense of dry sarcasm and biting comebacks. A typical Vulcan would just react with incomprehension or excessive literalism when a human says something illogical or impertinent, but T'Pol will wither them with a sardonic reply. Maybe it's more "wit" than "humor," but it's definitely there.

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I can agree with that. Back to the original question of getting a good laugh, you might get a giggle or two from talking to T'Pol but not a good laugh. Whether or not it would be entertaining to try to get her to laugh, it would probably get frustrating quickly since, unlike the Buckingham guards that would want/enjoy a good laugh, you would never succeed with T'Pol.

The best third season of a Trek series? It would have to be TNG. The show really pulled it together during this season, which culminated in the first half of The Best Of Both Worlds.

DS9's third season was a close second, but that series didn't really get good (IMHO) until the fourth season.

The best funny person to hang out with? After giving this some thought, I would have to go with T'pol, too. I recall a really funny moment in Enterprise where she was making one zinger after another (in complete deadpan fashion) with Archer and the others all expressing shock and joy.

I need to hang out with someone who wants to try all the Trek drinks so T'Pol is out. Drinking green tea doesn't do it for me.

I think I'm going to have to go with Quark. He's funny, flirtatious, has hundreds of stories and experiences to relay and knows how to have a good time. He's super interesting AND our drinking session will not get interrupted by his comm badge shrilly telling him to report to the bridge.